The key moments, with employee sentiment along the way.
2013
🌱
2013
Founded in Atlanta
Tope Awotona pours his savings into a simple idea: a link that kills the 'when are you free?' email chain.
Wikipedia
Jan 2021
📈
Jan 2021
The peak: $3B, almost overnight$3B
Largely bootstrapped for years, Calendly takes a $350M round at a $3B valuation as remote work makes the scheduling link ubiquitous.
CNBC
2023
💔
2023
Slips out of the club (on paper)
As the SaaS boom cools, PitchBook's model marks the private company at about $793M (end of 2025) — roughly 74% down and below the $1B line, though no down round makes it official.
PitchBook
2023–24
💬
From the inside · Glassdoor reviews, 2023–24
Glassdoor reviews from 2023–24 described the reset from inside: internal equity units that had lost most of their value were cashed out while underwater, a 2023 workforce reduction, and perks and stipends trimmed as the boom-era cushion faded.
Jun 2026
Jun 2026
The face of the SaaS fallers
CNBC's report on PitchBook's 220 fallen unicorns leads its SaaS section with Calendly; its table puts the company at $793M, 74% below the 2021 round.
CNBC
💬 entries paraphrase anonymous, unverified reviews posted publicly on Glassdoor ↗; dated facts carry their source.
How it happened
Calendly is a US scheduling-software company that raised at a $3B valuation in early 2021. As the SaaS funding boom cooled, PitchBook's model put its value at about $793M at the end of 2025 — roughly 74% below the 2021 round — and CNBC led the SaaS section of its fallen-unicorn report with the company. As a private firm that has not raised since 2021, the markdown is an external estimate rather than a priced round.
Source: PitchBook model estimate as of Dec 31, 2025 (CNBC's fallen-unicorn table, Jun 2026), not a priced round
